


Too Many Tardies

by majesticduxk



Category: Supernatural
Genre: Daddy Kink, Dean Is A Good Boy, Domestic Discipline, Established Sam Winchester/Dean Winchester, Feminisation, Hand Spanking, Humour, M/M, Over the Knee, Pet Names, Spanking, Strapping, Sub Drop, Sub!Dean, Team Dean's Red Ass, Top!Sam, belt, bottom!Dean, d/s verse, dd office environment, dd verse, dean is spanked by everyone, erotic spanking, hole spanking, one punishment is triggering for Dean however he did not disclose, paddles, punishments have been agreed to before hand but it not really addressed in this story, structural dynamics, there is no safe wording in a dd environment
Language: English
Status: In-Progress
Published: 2019-11-27
Updated: 2020-10-17
Packaged: 2021-02-25 21:15:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 11,564
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21582097
Author URL: https://archiveofourown.org/users/majesticduxk/pseuds/majesticduxk
Summary: Where Dean works, office discipline is taken Very Seriously. You’d think that would be enough for Dean to be on time, wouldn’t you?
Relationships: Dean Winchester/Sam Winchester
Comments: 150
Kudos: 329





	1. Late for work... Again

**Author's Note:**

  * For [Deadmockingbirds](https://archiveofourown.org/users/Deadmockingbirds/gifts).



> a/n I don’t even know how to describe this one. An office dd environment which is part of a wider d/s verse? All I know is I wanted to write LOTS of Dean getting spanked and this is what I came up with. And I have just been sitting on this, but it’s the WONDERFUL deadmockingbirds birthday today (she kept that one quiet…) so, Mock? Have some spanking goodness <3 This is part 1 of… probably 3 or 4. Let’s see where that goes. 
> 
> This is not beta'd. I do not own the characters. There's gonna be a lot of spanking. 
> 
> for anyone who is not okay with spanking: don't read. This is not considered dub con as it is normal in the universe (dd and d/s), and the rules are established and people agree to them. Thus there is no coersion. There is no dubious consent. And if that is not your cup of tea, but you are sad as my writing is so amazing, I have so many fluffy things, that you are sure to find something charming there.

The very epitome of cool, calm and collected, Dean Winchester kept his eyes straight ahead and strode across the foyer at 9.10am. He was dressed just a little fancier, his expression was just that more confident, and in front of him the elevator stood, doors closed but the little light gleaming _G_ was enough to keep his hopes up: it was on the ground floor, ready to whisk him away to safety. Dean was so stressed he couldn’t even smirk at the idea of his oft hated cubicle being a place of safety. He wasn’t there yet. If only he could reach it without being seen… 

_Don’t lose focus_ , he warned himself. _You've got to fet there. You’re not safe yet_.

Normally Dean could deal with being late. But recently something had changed… the wry smiles and headshakes had given way to stern brows and… and while he hadn’t been bent over his supervisors desk - _yet_ \- his book was a hotbed of tardies. Heck, he’d been written up seven times week for being late, and it was only Thursday! How did he manage to be late more than once a day

Dean’s buttocks clenched involuntarily. His boss’ eyes had promised retribution on the next occasion. It would definitely be in the best interests of his ass to make it to his desk before anyone saw him.

Speaking of which… Subtly, Dean let his eyes drift to his right, and _yes_! Dean did a silent fist pump. The concierge desk that was manned from the moment _Milton Industries_ opened to the moment it closed, the desk that monitored the single entrance into the building, the desk that was one of the banes of Dean’s life, was currently empty. 

Perhaps the fates were on his side! 

With a new, real confidence in his step, Dean headed towards the elevator. And it was right there, right in front of him. All he had to do was enter. And then make it to Floor 22. And then to his desk, which was- _one challenge at a time, Winchester_ , Dean cut off his spiralling thoughts. He could only do one thing at a time. He couldn’t second guess or falter. That way lay failure.

Looking neither right nor left, Dean walked right up to the elevator and reaching forward, Dean hit the up arrow, and - _yes!_! The door opened immediately. Quickly stepping inside, Dean hit the 22, only daring to breathe a sigh of relief as the doors closed behind him.

“I think you’ll find Floor 50 is more appropriate at this time of the morning.”

To say that the voice was a shock was no understatement. And the fact that he didn’t piss his pants was but a small mercy. By the time his vision cleared, his heart rate returned to normal, and his mind had caught up with his body, the result was the same: Dean was totally fucked. 

Schooling his features, and donning his most innocent expression, Dean turned to face the owner of those words. It was Castiel Milton, one of the six owners of Milton Industries. Dean hadn’t had a lot to do with any of the owners, but rumours… rumours said that Castiel was the gentlest of the lot. Maybe he could talk his way out of this? 

“Good morning, Mr Milton. My desk is on level 22, and the sooner I get there, the sooner I can do my best work for Milton Industries!” 

Dean infused his voice with enthusiasm and earnestness. Castiel gave him the tiniest of smiles. It might have even been friendly. Why then, did it feel like a threat?

“That would have been appropriate, Mr Winchester, had you joined us ten minutes ago. As it stands, we will be meeting with the other directors shortly.”

Dean gulped. He was right - that smile was a threat.

~o~

Castiel kept the pleasant smile on his face. He’d been told it was terrifying, and if Winchester’s eyes were anything to go by, that was true. Not that this brought him any joy. Dean _was_ an excellent worker. He went above and beyond what was asked of him.

However.

The man couldn’t turn up on time to save his life. Normally, Castiel would have been happy to give Dean a pass on this. And not just because of his pretty face and shapely behind. Castiel applied the rules fairly to everyone.

Had it been left to Castiel, a sharp word, a little more direction and a lot more supervision. That would be the punishment of choice. But that was not in Dean Winchester’s future. Dean's direct supervisor had failed in his duty, by allowing Dean's deriliction of duty without reigning him in. Adler would be dealt with, and so would Winchester. The board had spoken and the board had determined that one Mr Dean Winchester would get his ass handed to him.

This morning had been a test, though Dean had not been aware of it. Castiel had argued it was unfair but his fellow directors simply pointed out that the work day started at nine. An employee should need no warning of this. After all, all employees signed the contract stating they understood the rules and the ramifications of not following them to the letter. 

And tardiness was not acceptable.

Although he had hoped otherwise, nine o’clock had come and gone with Mr. Winchester nowhere to be seen. As directed, Adler had checked in not a moment after 9.01 and Castiel had quickly coordinated his fellow directors. Not that they’d needed any coordination. All of them – even Gabriel – were already in the boardroom, awaiting his and Winchester’s arrival. Shaking his head, Castiel had to hide a smile - a real one this time. Not a single Milton had thought Dean would make it to work on time. And Winchester hadn’t let them down. Or rather, he had let them down, which mean he hadn’t let them down… No, he had let them down, let the company down. The fact that they all looked forward to it was coincidental and fed right into their plans was beside the point.

Leaving that convoluted line of thinking, Castiel cast his eye over his unhappy employee. The long trip had given him time to think (Castiel was certain that one of his brothers had slowed the trip from floor 40 to 50, to give whomever was coming up time to… think), and now that the initial terror had vanished, Winchester’s mind was working overtime. It was fascinating, watching his mobile face: annoyance, disdain, and even a smirk crossed his features. (Castiel would bet his own ass that that particular expression was related to Adler). Smart as he was though, there was no escaping his fate.

~o~

Shifting nervously on his heels, Dean was pretty sure he wasn’t going to get out of this one. He’d been living in a fool’s paradise, as day after day, week after week, even with his pretty much _constant_ tardiness he’d managed to avoid more than a few spanks bent over someone’s thigh. And _maybe_ Dean was lax because of it, but he stayed late which should have made up for it! He got everything done... but no. That didn't matter. He knew the rules, and the frustrating thing? It was his own fault! Although… _heh_... maybe Dean’s asshole of a boss would find himself in the firing line too? Dean hoped his smirk was on the inside, as he thought of Adler’s fate. Surely Adler would get his ass handed to him too, for not doing anything? 

The pleasant thoughts were washed from his mind as he met Castiel Miltons’s gaze. Milton was staring at him unblinking. And yeah, rumour had it that was just his expression, but somehow Dean knew the current look spelt trouble.

Time to put some fires out...

“I… I’m very sorry Mr Milton. It won’t happen again.”

“Yes, Mr Winchester. I am sure it will not.”

Without breaking eye contact, Castiel reached forward, and into Dean’s top pocket, removing his Little Red Book. 

Fuck.

~o~

The Little Books were unique to _Milton International_. The business itself had a reputation for being warm and friendly (a few of the family notwithstanding!), the hours were good, the pay reasonable, the support and services wonderful, and there was lots of efforts made to accommodate every employees needs. But the few _guidelines_ there were, were enforced with an iron rod.

Literally.

One of the things Dean had made sure of (well. Sam, but Sam was the researcher) was that dom’s couldn’t abuse their power. In many workplaces, subs ended up in terrible positions - and yeah, there were so many potential puns there - with no recourse whatsoever. _Milton_ didn’t work like that. Everyone who broke the rules got punished. And that meant _everyone_. 

Every single employee at _Milton_ got their little book: subs got a red book, doms a blue book, switches were purple, and A-dynamics were yellow. Part of the induction package was the negotiation of acceptable work punishments: a sub’s punishments were generally negotiated with their dom (and Dean had been incredibly upset with Sam. Especially with the clause that all of Dean’s punishments should be reported to him. Dean’s ass clenched again. Sam wasn’t going to be happy…), while dom’s tended to negotiate their own punishment. Switches and A’s were on an as needs basis, but everyone agreed, the process was fair. Once this was signed and on record, unless you renegotiated, there were prescribed disciplinary measures. The actual disciplinary action decided upon by whoever administered.

Although most punishments were fairly standard. Infractions generally earned you a spanking, although the particulars up to the spanker. For anyone under management level, the direct line supervisor administered the punishment, and it wasn’t unusual to see people walking very carefully, or with tear stained faces. Disrespect earnt you a bare-ass spanking with the added humiliation of walking around with a red ass for the rest of the day.

Though a spankee might have got a few sympathetic glances, it wasn't hard to not get a spanking. The rules were pretty straight forward: Tardiness. Untidiness (worse if in front of a client). Rudeness to a client. Rudeness to a superior (although discussion was ok and even encouraged, just be sure to ensure they remained heated). Abuse of Power. Unfairly influencing a sub.

It was all common sense and no one had a problem with it. Dean certainly didn’t. At least not up until this very moment. 

Despite the fact that his direct boss was a dick, Dean was good at keeping a straight face and holding his tongue. So though he’d earned a few spanks for being late, and one memorable belting for (in Anna’s words) _dressing like a street urchin at an important client meeting_ , he’d pretty much kept his nose clean and his ass lily white. At work at least. 

Although judging by the slow way Castiel was thumbing through the book, not as clean as he thought.

“You’re a good employee, Dean. We appreciate all the work you do. However.”

Fuck. Castiel was going to spank him in the elevator. He could feel it. Taking a deep breath Dean tried to mentally prepare himself.

He seriously wasn't ready for this.

“But this book is full of the minor infractions too. Infractions where a spanking _could_ have been administered, but it was chosen to take a different route.”

Okay…?

“In the last six months, Mr. Winchester, you have been written up 64 times.” Dean went to interrupt, but Castiel caught him in a cold stare. “I don’t think you want to add insubordination to today’s punishment, do you?”

Dean settled, mumbling a slightly resentful “No, sir.”

“Late for work. Late for a meeting. Borderline insubordination. Disrepecting the-“

The list was distressingly long. Although he was _sure_ he hadn’t been written up that many times! There was only one possible cause of this: Adler had been doing the dirty on him! They weren’t supposed to do that, write in the books willy-nilly. There was mean to be a discussion! It was supposed to be straight forward and transparent and-

“-really the time to not listen to me?”

Shit. Dean’s eye flew to Castiel’s and he looked disappointed.

“I was hoping to go easy on you, Dean-“ Dean’s heart didn’t even bother leaping. He could hear there was a _but_ in that sentence, “but this just confirms that you need some firmer handling.”

The elevator bell rang, and a very firm hand was placed on his shoulder. “This way if you please, Mr Winchester.”


	2. The Boardroom

**Summary for the Chapter:**

> It's time for Dean to face the directors. 
> 
> Kinda?

**Notes for the Chapter:**

> ahhhhh. You know, I thought I had an idea for this fic. I mean, I did, I do. But at the same time, when I just got stuck on chapter 2, I jumped write over and started chapter 3... and chapter 4... and have just now finished this chapter. What it means, is that the next two chapters will come more quickly, and while chapters 4-8(ish) will be slower, there is more of a plan. 
> 
> This chapter talks a lot about chairs. And you know what? I'm not sorry. I tried to write them out, and they wrote themselves right back in. 
> 
> So, uh. Enjoy?

It wasn’t often you got invited to the boardroom (heh. _Invited_ , Dean was hilarious), and despite his completely justified terror, Dean couldn’t help but be a little intrigued. 

_Milton Industries_ was an old school organisation, which really meant a long history and old money: anybody who was anybody had been a client for years. Great, great grandfather Charles Milton had started it back in the days when only doms were in the workplace – from the boardroom to the janitors closet, only doms stalked the hallowed hallways. Of course, the world had come a long way since then – doms could still be cleaners, but now subs could stalk the boardroom. Even Dean, as a sub, was quite high up in sales. While he wouldn’t have gotten his foot in the door without affirmative action, he wouldn’t have placed or been promoted if he couldn’t hold his own, thank you very much! 

…Or if the organisation hadn’t been open to it. Yeah, there were ways to keep subs locked out. But _Milton_ ’s made a point of being an equal opportunity employer, and there were plenty of subs in all sorts of positions, including in the leadership. Sammy had made sure of that before he let Dean work there. 

Still, it was still a company with history. And wealth. And that attracted all sorts of rich and important people. Rich and important people the company wanted to impress. 

In keeping with this, the foyer, which was still the original design, was all understated elegance. Soft, glowing, granites and marbles allowed every client – new and old – to be subtly reminded of the sort of place _Milton _’s was: Rich. Trustworthy. _Milton_. It also reminded the employees they were part of something big and grand. __

__And – as Dean had been reminded just a few short moments ago – every single person who came to _Milton_ ’s had to walk through that foyer, so each and every time they were reminded of just what _Milton_ ’s was. _ _

__At least that was the foyer. The offices were for the workhorses, so they were comfortable enough (it’s hard to work when you can’t get comfy, and no, a spanked bottom didn’t count. Dean had had that conversation at work _and_ at home), they were somewhat spartan and utilitarian._ _

__The boardroom though? It was the home of the company’s owners, the Milton’s, who just happened to be some of the most powerful people in the world. And given that every generation of Milton’s had supposedly added… well, you heard whispers, of how amazing it was._ _

__So while Dean didn’t know what to exactly expect, the privilege and indulgence was really no surprise_ _

__It was still amazing though._ _

__Dean’s eyes skirted over the wall art (because if this was a test, no way was he going to be caught oogling at the tentacle porn, no matter how intriguing), and out of the corner of his eye he could see flashes of gold and – Dean couldn’t stop his head swivelling - rubies? Did all those octopus’ statues seriously have rubies where their suckers would be? What the fuck?_ _

__It was too much wealth. His commoner mind couldn’t deal with it, and instead his eyes drifted away from the glitz and glamour to the cream carpet (in the privacy of his overloaded brain, Dean couldn’t help but sneer. Only truly rich people who could pay other people to clean had cream carpets).But… it was beautiful. It was so pretty and shiny, and even through his shoes the carpet felt plush. How the fuck did it feel soft through his shoes? It might be softer than his mattress, and it was memory foam! Maybe he could-_ _

___Focus, Winchester!_ _ _

__He needed to pay attention. Castiel had already reprimanded him for his lack of focus he really, _really_ needed to focus now. _ _

__Taking a deep, calming breath, he allowed his eyes to take in the boardroom table (and fuck, what the fuck was it inlayed with? Mother of pearl? _opals_ ) and the five shadows surrounding the table. Chairs, he thought. One for each of the Milton brothers. Well, not all of them. Rumour had it there were many more Miltons, but no one had met more than the five that were presumably present in the room. _ _

__Now that he thought about it, those chairs were pretty fucking huge. Even though he craned his neck (only slightly, because Castiel’s hand was still on the back of his neck, and fuck, that was right, Cas was still on his ass…), he couldn’t see any bodies._ _

__Just the five empty chairs._ _

__They were covered in rich fabrics that looks soft and amazing, and there were pillows. They looked perfect to curl up in, the timber curved and welcoming. Except –_ _

__Dean was pushed down onto a hard seat. He could only imagine what it would feel like on a freshly spanked behind. Castiel’s hand squeezed hard in warning, before he let go, and walked around the table to his seat. Green pillows, Dean noted absently. Dean’s eyes cast once again over the chairs although -_ _

__

__“Holy fuck, is that a throne? Is that real gold?”_ _

__A small man popped out from behind his chair, throwing himself down before removing a sucker from his mouth. Then he winked. “Sure is Dean-o!”_ _

__Flushing bright red, Dean opened his mouth to speak, but it appeared to be a sign. The three remaining Miltons emerged from behind their chairs, and Dean could barely breathe: Michael, Lucifer, and Raphael in the flesh. Michael and Raphael gave Dean a disapproving look before seating themselves, while Lucifer smirked as he lowered himself onto silver pillows._ _

__Then all of them (except Castiel) pulled hooded robes off their chairs, and proceeded to stare at him._ _

__What the fuck? No, seriously. Who the fuck had hooded robes? Drama queen. Which meant that they. Were. Drama. Queens. Each and every one of them._ _

__“Fucking drama queens.”_ _

__Dean felt himself relax, before Castiel’s stern cough automatically forced his back straight. Shit! Did he say that out loud? Even if they _were_ (and he was allowed to think that in the corner of his own mind), they were still the bosses. And he _had_ been called up here to get his ass handed to him. And now his mouth was going to get him into even _more_ trouble._ _

__As the silence stretched, Dean’s mind started to wander. How was this going to go? It was pretty serious getting called up in front of the board. He couldn’t even remember the last time anyone got hauled up in front of the board... Oh wait. He could. Three years ago, Laura from Accounting. She’d been out the whole day, but every time she was seen she looked miserable._ _

__Would he look as miserable?’_ _

__And really, three years? Everyone here was that well behaved? No… no, that was impossible. There must have been other people. Shit! Maybe they were a secret society, and they lured unsuspecting victims up here to murder and-_ _

__“Thank you for coming, brothers. As you know, Dean Winchester is a wonderful employee. Helpful. Polite. Skilled even. However, his tardiness is unacceptable.”_ _

__Trust Cas to bring the mood down. Still. It stopped his spiraling thoughts._ _

__“Has he been reported before?”_ _

__Dean’s eye’s flickered to the new speaker. Michael Milton, oldest brother and president. Eyes shadowed by his blue velvet hood. Dean quickly glanced at Castiel, whose face was mask, but whose eyes… hah! Sam got that look too! Completely exasperated, but couldn’t do anything about it._ _

__And that, more than anything, told Dean he wasn’t about to be murdered._ _

__With a lighter heart, he tuned back in to the proceedings._ _

__“…does that work for you, brothers?”_ _

__Shit! Why couldn’t he have had his epiphany a few moments earlier?_ _

__~o~_ _

__“You will come directly to my office, and be present by 9am. I will punish you, and then I must go. Unfortunately you can’t come with me-“_ _

__What??? Why would Dean be going with the director?_ _

__“-as I will be away for quite some time, however, next week you will start with your shadowing duties. And they shall administer discipline as necessarily.”_ _

__Dean probably looked confused. He felt confused. What did that mean?_ _

__“You are being punished for being tardy, Dean, and we feel that spending some special time with each of the directors will help to keep your mind on task. Now, we’ve each reviewed your red book, and will adhere to all of the rules your dominant has prescribed-“_ _

__“Which isn’t that many.”_ _

__That was Cas, sounding disapproving. Well, fuck Cas! Dean’s book was legitimate. At least… looked legitimate. Fuck. Fuck. If Sam found out Dean had it altered, Dean would be seriously screwed._ _

__The directors started arguing with each other, until Michael cleared his throat._ _

__“That is all, Dean. You have received your instructions, and will be expected to report as required. Unless there are any questions, you may go.”_ _

__“No questions, Mr Milton,” Dean murmured at Michael._ _

__“Ah, ah. First names, Dean. With so many Miltons it’ll get too confusing.”_ _

__What? He couldn’t call the directors by their first names! That was too weird, but there they all were, nodding away._ _

__“Ah, yes, okay. Okay. I will… I will go.”_ _

__“And I will see you out.” Castiel was out of his chair, and at Dean’s side._ _

__As the lift doors closed, Dean was sure he was in shock._ _

___What the fuck had just happened?_ _ _

__~o~_ _

__When Castiel returned it was to Gabriel shaking himself._ _

__“It’s called a happy dance, Cas! That went so fucking well! It’s exactly as planned!”_ _

__“Gabriel!”_ _

__Gabriel stopped his shaking. “What? Am I wrong?”_ _

__He looked around the room before gesturing dramatically at his brothers. His hood dropped back at the perfect time. “Well, am I?”_ _

__Raphael sneered. “I’m unmoved. I think there are easier ways to deal with minor infractions.”_ _

__“Luckily it’s not about you. Or even about infractions. It was just perfectly timed to just fall into the master plan. Either way, I’m looking forward to getting that cute little butt in my office.”_ _

__“Lucifer!”_ _

__“What? As if you’re not. Well… except for Raph, and Gabe who don’t-“_ _

__“No way! I’m looking forward to this too!”_ _

__Gabriel’s interjection caused the room to fall silent. It was Michael who spoke._ _

__“Gabriel? What?”_ _

__Settling back on his throne, Gabe smiled at his brothers._ _

__“It’s the strangest thing. You know my dynamic, and where I fall. And while I’m not sure stranger things have ever happened, I’m actually looking forward to getting Dean bent over my desk.” Reaching for Dean’s work contract, Gabe flicked through. “It’s a real shame his dom doesn’t allow sexual discipline, because I’d like to-“_ _

__“ _Gabriel!_ ”_ _

__Gabe chuckled at his brother’s – all of them - shock._ _

__“What? It’s a dynamics thing. I’ve had to punish people before – doms _and_ subs. It’s part of the job. But this?” Gabriel’s grin was not friendly. “This is just the first time there’s ever been a big enough difference in our orientations for me to feel dominant. And I kinda like it.”_ _

__Gabriel drifted off into some sort of weird daydream, but it was Lucifer who broke the tension._ _

__“Really? No sexual punishments? For somone with Dean’s rating? Give me that. Surely that’s wrong.”_ _

__

__Even as they all reached for Dean’s contract, Castiel let the discussion of Dean’s punishments – or lack of them- wash over him. He already had a plan. He also knew that this next month would be very interesting, in more than one way._ _

**Notes for the Chapter:**

> Thanks for everyone who as checked in <3 <3 <3 
> 
> I have been insanely busy, with no internet. But I have missed writing, and missed you all!


	3. RaphAel

**Summary for the Chapter:**

> The first director

**Notes for the Chapter:**

> This whole chapter came about because of Mock's throw away comment about 'oh! A dynamic? I look forward to learning more' and thus I felt I must educate *bows* I've added a few more tags (although only sub drop is relevant for this chapter). You have been warned/enticed, depending on what you like.

“Ah. So you can turn up on time, Mr. Winchester.”

Day one of… whatever the hell his life had become, and Dean just _knew_ he was going to be sick of those words. 

Any smart response he may have had died on his lips as Raphael took Dean’s little red book from his top pocket. He was about to get his ass handed to him, and didn’t want make it worse. Dean could stand here and be good and quiet and obedient. 

Although the longer Raphael took to flip through his book, the harder it became to say nothing. Because seriously? Dean’s legs were actually starting to ache. Casting a subtle, yet sorrowful, look at the chair just inches to his left, Dean let out a silent sigh. It was obviously part of a test, and Dean had failed enough of those recently.

But still. Raphael could have _said_ something. 

With nothing else to do, Dean's eyes wandered. Raphael's office was plain. Kinda like Dean's cubicle, except nicer materials: a real wood desk, an extremely comfy looking chair, and a pen that you dipped in ink. If that was class, they could have it. 

That took all of five seconds to look at, and that remained was Raphael Milton. Dean's eyes crossed as he anaylsed each expression that crossed the directors face. Every time Raphael’s lips turned downwards – which happened with alarming regularity – Dean winced. A few times, Raphael picked up his pen, slowly dipping it in that stupid ink pot then _tap tap tap_ before making some notes. Dean craned his neck, but couldn’t read the words. 

After way too long, Raphael put Dean’s book, and the pen, down. 

“Sit.”

Dean obeyed with alacrity. Hard, his butt noted. And it would probably feel even harder on a freshly spanked backside. Suddenly Dean had a very good reminder of where this was heading. 

“As you are aware, at the boardroom meeting it was decided that you would be the responsible to each director for one week. For that week, you are required to do exactly as you are told, be that shadowing, new jobs, ferrying clothing, buying flowers. Anything and everything. You are required to follow each and every rule, and that for the time you are allocated to them, that Director is also responsible for your discipline.”

Oh…. That was what they meant. Dean had been pretty confused when he left the boardroom yesterday (it was probably all the gold in the room, messing with his sense of space and time), so he was grateful to Raphael for spelling it out again. 

Kinda.

Raphael frowned, and Dean sat up straighter. A frown was never a good look when it was directed at him, and Raphael had already frowned a lot. 

“This was not my preferred option. I would have had you arrive here at 8.30 sharp, paddle your tardy behind, then send you back to your office.” Raphael’s eyes flicked over his notes. “Of course, there would have been an evening reminder as well.”

Yikes! This person was as stern as Sammy! 

“Unfortunately, the board had other ideas, and even had they agreed with me, I am about to leave for tour of our overseas offices. This has meant I am required to go first as I will not return until after your punishment has concluded.”

The serious man stopped before leveling Dean with a look. “At least, for your sake, I certainly hope your punishment has concluded.”

Gulping, Dean attempted to look both angelic and capable of turning up on time. Raphael wasn’t joking!

“As it is, I only have half an hour this morning. So for today only, you will be reprimanded then sent to your office. Now, I’ve read through your doms’ prescribed punishments, and while I would never judge anothers relationship-“

This was a lie, he was so judging!

“-I’m very surprised that your dom doesn’t need to be informed when you receive a punishment. Any punishment.”

Thankfully Raphael had turned back to Dean’s book. And also thankfully just yesterday Dean been reminded of his foray into forgery. Jesus, it had been years - _years!_ since Dean had gotten a little pissy at Sam’s stupid restrictions. It wasn’t like he _wanted_ to be punished, but he wasn’t a baby, dammit! And so he’d changed Sam’s guidelines, and while he was at it, he’d changed Sam’s request to be informed when Dean got in trouble. And that was just because Dean was a big boy, totally capable of managing his own discipline, and not because Sam was a literal pain in his ass when someone else punished him. Definitely not. 

So it wasn’t like Dean _regretted_ making those changes. It was certainly making his life easier right now! It was just… if Sam ever found out that Dean had circumnavigated him like that, Dean would probably never sit again. 

“Mr Winchester.”

Oops! That was the voice of someone who was repeating themselves. Straightening up, Dean gave Raphael his most steadfast gaze. He wasn’t about to discuss his contract. That would involve lying, so Dean deflected with the truth.

“I’m sorry, Mr Milton.” Shaking his head, Dean corrected himself. “Raphael. I’m sorry, Raphael. I will of course take whatever discipline you deem necessary.” 

Dean lowered his voice, let his eyes shimmer with unshed tears, and went in for the kill - he wasn't the best in sales for nothing! 

“I’m just nervous. I know I deserve this. But it’s just so-" Too much? Time to tone it back. Squaring his shoulders, Dean faced his one man firing squad. “I’m sorry, sir, I know I deserve this, and I await your directions.”

Did Raphael’s face soften, just a little? 

“I need to leave in 30 minutes, which will give me just enough time to deal with you.” Raphael held out one imperious hand. “Now come here.”

~o~

Raphael was all business. And while Dean was used to all business, something felt off. He ignored that stupid part of him (probably just because it was a big boss), and Raphael quickly had Dean’s trousers and blue panties (ugh! Damn Sam and his infernal preferences) and then Dean directed to bend over the desk. To Dean's left was his Red book, with a page of notes beside it. He still couldn’t read the frigging thing, but he could see the beautiful penmanship. To his right, was a small paddle. It didn’t look that bad, but, as he had learnt on more than one occasion, looks could be very, very deceiving. Sighing, he bent over, and assumed the position. 

Or at least, tried to. Stretching his fingertips out, he over shot the desk, Which felt weird. How was he supposed to brace himself if he was just kind of flopping around? Still, with that paddle so close to his bared behind, it really didn’t seem the time to ask about it. 

Instead he just gripped onto the edge of the desk, and braced himself as best he could. 

Still, it was pretty weird. Maybe Raphael’s sub was much shorter. Perhaps, for a short person, this really was an uncomfortable stretch. Now that he thought about it, Dean didn’t really know much about any of the directors subs. Or doms. Partners? Seriously, why were there no rumours? 

The intriguing musings were interrupted by the _thwack_ of a paddle across his bared ass.

“Ow,” he complained, more out of surprise than anything. Because, despite Raphael’s strong appearance, there wasn’t really a lot of power there. 

At Dean’s cry, the paddle came to rest on his buttocks. 

“Did that hurt?”

And holy fuck, what the fuck? There was a real note of uncertainty in that voice. 

“Uhhhhhh…” Dean wavered. There was no point in lying, and yeah, it had _kind of_ stung, but that was the whole point of a punishment. Right? “Uh no, sir. It didn’t really hurt. I was more surprised.”

Behind him Raphael let out a relieved breath. “Good, that’s good.”

Dean shuffled into a more comfortable position, waiting patiently for Raphael to get back into it.

“What’s your colour?”

 _What_???

~o~

Ten very light spanks later, Dean was still wondering what the fuck was going on. 

It hadn’t hurt. He'd bet a month in chastity that his ass would look no different by the time he got home. Not that that was a great bet. If his ass _was_ still red when Sam got home, that's exactly what would happen. Sam. His beautiful steadfast Sam. Sam wasn't confusing. Firm. And strict. And obsessed with Dean's ass. But not confusing. If Dean kept thinking about Sam, he could ignore how dizzy and light headed he was. Which was also weird, but the whole encounter had been very weird. 

Pulling up his pants, he turned to ask the director if that would be all, only to find Raphael wringing his hands. 

_Did people actually do that_? 

“Pale. You look pale. I’m sure you look pale, and I need to do something about that, but I really need to go.”

Dean attempted to use his sternest and stablest voice. “I’m fine, sir. I’ll just head back to my office, since you need to be on your way.”

At least, that’s what he attempted to say. For some reason, Dean couldn’t find any words. Combined with his dizziness, it was kinda like he was dropping, but there was no way he was, because he was Dean ‘buns of steel’ Winchester. Sammy spanked harder than that with his bare hand! 

Raphael appeared to come to a decision. 

“I need to leave, _and_ you need someone. I am not the right someone. Dean, sit down on that seat – no, the one with a pillow, and someone will be here presently.”

And then he left. 

He... left.

Because of Dean? What had he done? He'd been good, right? He'd done everything Raphael had said, and he hadn’t complained, he’d even taken that tiny spanking and thanked the director for it. But Raphael didn’t say he could go, and then he left. That must have been Dean’s fault, but he just didn’t know what he did-! 

Vaguely Dean heard a door open, and fragments of a conversation

_”Raphael!”_

_“… didn’t know…”_

_“… must tell him…”_

And then he wasn’t exactly sure how it happened, but next thing he knew Dean was on his knees and someone was running their fingers through his hair. That felt nice. But it wasn't Sammy. The knee was the wrong height. Does that mean he shouldn't be here? Who was it? Was it someone he had to kill? 

They probably weren't too evil, not if they knew how to stroke a head so nicely. But who was it? When he stopped to listen, Dean noticed there was a deep hum. Words. Those sounds were words. Who did he know with a deep voice? Castiel? Was he leaning against Castiel? Why would Cas be here? That meant he was in the wrong place, and he should move, but but he’d just rest his eyes a little longer. Can’t get in trouble when you aren’t causing trouble, right? 

Wait. That didn’t make sense. Dean decided not to think anymore and just let the fingers scritch at his head. 

Which is of course when the fingers stopped moving. Dean chirped a complaint and the buzzing words became a deep, beautiful laugh. It _was_ Cas. 

“Back with me?" 

Of course Dean was. He’d never gone anywhere. He just wasn’t sure he wanted to move. But the boss made a good point. He did have to get back to work, so it was with more than a little regret that he nuzzled against the knee, before sitting up and slowing opening his eyes. 

The world wasn’t as bright as he expected. Actually, nothing was as he expected. The room was... kinda sexy. Dark wood, and reds, and more of that soft carpet from yesterday. It wasn't rich dick cream though. It was lush and green. This definitely wasn’t Raphael’s office. He really had to get out of there. 

“Uh, uh, uh. You’re not going anywhere yet. We need to have a chat first.” 

Dean tensed. That really didn’t sound good, but he forced himself to take a deep breath and relax. He wasn’t sure what he did wrong, but time to make it right. Ignoring Castiel’s disapproving _Dean!_ , Dean sat back on his heels, and squared his shoulders. 

“I’m very sorry, sir. I take full responsibility for…” Damn. It was hard to apologise when you weren't quite sure what you did. He couldn’t apologise for dropping. If Sam heard about that who knew what would happen? Probably therapy, and lots of it. 

Luckily Castiel jumped in. 

“Dean.” 

Except he still sounded disappointed. 

“No member of the company - dom, sub or other - will ever be required to _apologise_ for their emotional distress. We have a duty of care, Dean, and you’re safety is important, and should you drop, like now, I will always take care of you. Now…” 

Castiel’s eyebrows drew low, and he reached straight for Dean’s Red book, which had been sitting all innocently on the short table next to Castiel. Why were they so obsessed with his stupid book? Castiel, like his brother, took his sweet time looking through. At least Cas could do two things at once and spoke to Dean. 

“Raphael has given me permission to speak to you. He would have told you himself, but he really did have to leave for a work trip, and oh... You really are a high level sub. That does explain a lot.” 

Well it didn't explain a lot to Dean! 

“Raphael is A-dynamic.” 

That actually explained a lot: the weird colour thing in the middle of a punishment, asking if it freaking hurt, but actually meaning it and not being a sadist. And Dean dropping… 

“But it wasn’t even a real punishment,” he complained. “Ten taps that I couldn’t even feel.” 

Castiel’s lips quirked. “Yes I am sure your naughty bottom is used to a lot more than that.” 

“-hey!” 

“But it was Raphael.” 

He didn’t have to say more. Dean kinda got it. It was kinda like when he’d tried to dom for a few years. The whole thing had been an unmitigated disaster, he’d not felt comfortable in the role. And his partners had picked up on that, creating this feedback loop of discomfort and… Dean shuddered. That was with him knowing the sorts of things a sub would _feel_. In the case of an A-dynamic, they didn't even have that. 

“Thank you for telling me.” Dean told Castiel seriously. “I’m sorry he was put in such an uncomfortable position, and, don’t worry, I won’t tell anyone.” Dean chewed on his list. “Although, Sam, my dom…” 

Castiel looked surprised. “It’s no secret, Dean. Raphael doesn’t hide it. He doesn’t speak casually about it, but it is no secret. Although…”

Cas trailed off and Dean knew he was about to ask about Sam! Time to save his own ass. 

“It’s okay, Cas. Thanks for letting me know, it’s really helped to settle me. I feel fine now, may I be excused back to my office?” 

Dean sent him the puppy dog eyes. Even Sam, who had had years to build up immunity, was unable to resist. 

“Uh, yes. Very well. Report to Michael on Monday morning. At 8.30 sharp.” 

_~o~_

Long after Dean had left, Castiel was still staring as his knees. 

_“Cas?”_

**Notes for the Chapter:**

> Apparently its international fanworks day.  
> Shout out to the creators and consumers - one hell of a team!


	4. Michael (Part 1)

**Summary for the Chapter:**

> Chapter 4  
> Summary: Dean spends the week with Michael. And Dean and Sam have some Daddy and Princess time. 
> 
> Specific chapter kinks and warnings: wincest, daddy kink, strapping, feminization, pet names,

**Notes for the Chapter:**

> This is Part 1 of the Michael chapters. It was meant to be in one, but then Dean and Sam decided to have sex and I thought... well, I will leave another author's note on the next chapter.

Dean pounced on his dom the moment he entered the apartment.

“Sammy! Guess what! One of the directors is A-dynamic!”

Sam ignored Dean until his shoes were neatly placed away and his coat hung up. 

“Yes. Raphael Milton,” Sam responded as he breezed on past. 

Less than impressed, Dean followed his brother down the hallway. 

“What? You _knew_? You didn’t think to, I don’t know _tell_ me or something?!”

“Of course I knew, Dean. I researched very carefully before I allowed you to work at Milton Inc.”

Sammy blathered on for a bit more bit more, but Dean was distracted, staring at his brother as he stripped off for the shower. 

“…how did it come up anyway?” ‘

Ignoring the question, Dean licked his lips and looked his brother up and down. 

“I think I’ve been a dirty boy, Sammy. Need you to clean me up real good.”

Sam rolled his eyes, but pulled his brother in for a searing kiss. 

“Time to get my dirty boy clean then.”

~o~

Dean was at Michael Milton’s door at 8.58am. Not early enough to stress, but not late enough to be disrespectful. Okay, so it was cutting it pretty fine. He’d to hustle, but it was before 9am _and_ he had his breathing back under control. 

As expected, Mr Milton opened the door at 9am sharp. 

“Ah, Dean. You can be on time.”

Dean barely stopped himself from rolling his eyes. They were all going to say that, weren’t they?

Ushering him in, Michael gestured towards a comfy chair. Dean eyed it with surprise: that was for him? Michael offered him a shark tooth smile. 

“I have you all week,” he informed Dean. “I have plenty of time to turn your naughty bottom red. But I think… I think we will play game.”

 _Ugh_. Dean hated games. 

_Lies _, his brain unhelpfully informed him.__

___I only like fun games_ he shot back. His brain was silent. At least they could both agree that Michael’s games probably weren’t going to be fun. _ _

__Clearing his throat pompously, Michael walked to behind his desk and turned his back on Dean. Which was totally a dick move – Dean already knew who had the power here. A little part of him, a tiny little bratty part, wanted to run up and kick Michael in the pompous ass._ _

__But Dean was a good boy._ _

__“As you know you are here to be disciplined for your unprofessional and unrelenting tardiness.”_ _

__That was a bit unfair, Dean thought. Yeah he was late, but he was extremely professional. And he always did his work… Maybe he could negotiate different hours? Would Sam be okay with that? That would mean Sam would find out –_ _

__Michael’s voice cut through his musing._ _

__“So you have a punishment for that at the end of the week. Fifty, with my strap, across your bare bottom. But this is the minimum, Dean. For this week you will be my assistant and you will earn yourself penalties and rewards. We will sit down and discuss this on Friday afternoon.”_ _

__Dean was immediately in negotiation mode._ _

__“You said penalties _and_ rewards. Does that mean the punishment can be reduced as well?”_ _

__Michael smiled his shark like smile again._ _

__“Oh this is going to be fun!”_ _

__~o~_ _

__Working with Michael was exhilarating. Dean was set to be Michael’s shadow, and at first thought he would be nothing more than a glorified PA, but no! He got to stuff. And not just stuff, real stuff. He went along to meeting, he offered ideas, he went along to lunch, but not before he suffered the humiliation of Michael taking him to a suit shop._ _

__~o~_ _

__It was obviously an establishment for gentlemen. The sort of fancy place Dean would never even notice. For one thing the name was too small and written in the same colour as the woodwork. For another…_ _

__“Michael,” Dean hissed. “This is not appropriate. I’m on the clock!”_ _

__The director didn’t even acknowledge Dean, just dragged him in the door. For half an hour Dean waited while Michael tried on suits. He was, Dean had to admit, a snazzy dresser. And now that he’d calmed down, it was his job. Glorified PA and all that. Settling in to make himself comfortable, Dean observed._ _

__Michael always looked good in his suits. They had a subtle glow that enhanced him. Dean watched as Michael tried and shapes and colours that didn’t look any different to his lower-class eyes, and then the ties. Dean notes one that matched his eyes, and he was a little more interested when Michael moved onto the interesting colours - the warm cream against his tan skin, pants which didn’t cling, but rather enhanced the rather nice ass that Michael owned (what? Dean was collared, not _dead_ ). _ _

__It all added up to some sort of magic act in which Michael looked more than he was. Once again, Dean was reminded of how tricky these Miltons could be._ _

__“Will that be all, sir?”_ _

__A owner was a simpering Dom, but maybe Dean would simper too if someone was dropping that much cash in his establishment.  
“Not yet. Three suits for my partner.”_ _

__What? Dean say up straight._ _

__“What? No!”_ _

__Michael just spoke over him._ _

__“We’ll start with three. Dean will model the styles and I will choose colour and fits after. I also want to see a selection of ties, pocket handkerchiefs, and trouser socks. Oh, and cufflinks.”_ _

__What the fuck? Dean had to shut this shit down ._ _

__“Mr Milton. Michael.” Dean said it as firmly as he could, but goddammit if there wasn’t a quaver there. “I don’t need these things, and it’s highly inappropriate and-“_ _

__“Nonsense, Dean.”_ _

__Damn asshole had a thing for speaking over Dean. _Especially_ when he was being sensible. _ _

__“You are with me for the rest of the week, and so you will have to, what is the vernacular? _Step it up a notch_.”_ _

__Not just vernacular, but finger quotes too. Damn Miltons._ _

__“The clients we will see for the rest of the week expect us to dress in a certain way, and since you will be meeting those clients, you too will dress to that standard. Now, we can do this the easy way, or we can do this the hard way. But we will get this done. Am I understood?”_ _

__Michael’s eyes flash and Dean felt his body automatically soften in submission. _Stupid body_._ _

__But no. No! He was made of sterner stuff than that! Dean forced his shoulders to square, and looked Michael straight in the eye._ _

__“Sir, I will gladly step down if that is required. I’m just an entry level salesperson on a… a temporary assignment. This, the suits, this is not appropriate. I must decline your offer.”_ _

__Michael looked delighted. “I do so love the hard way!”_ _

__~o~_ _

__“and high end clothing shops have fucking _spanking horses_ hidden away! And then when massively rich assholes ask where they are, they just appear!”_ _

__Dean was complaining and Sam – a moderately well off asshole – was laughing at him._ _

__While Dean hadn’t exactly come clean, he’d told Sam he was acting up – as in a higher position, not misbehaving! – and so had to go shopping for new clothes. And Sam, the bastard, was laughing at him!_ _

__“I mean sure, it was velvet lined, and pretty comfy, but it was still a spanking bench. And Mr Milton just undid my pants, and spanked my bare ass a few times-“_ _

__Sammy wasn’t laughing anyway. He was frowning his dom frown. Shit! What had Dean done?_ _

__“How many times, Dean? Was it less than twelve or more?”_ _

__Ahhhh. Dean knew where this was going._ _

__“It was eight or ten. He didn’t get me to count, but this ass,” and yeah, Dean may have flaunted his behind a little, “can take more than a few love taps. And that is so not the point, Sam! He was being unfair!”_ _

__Sam’s tension eased, and he pulled Dean down to the bed and across his lap. He then pulled down Dean’s pants and subject his ass to a thorough inspection. Dean just relaxed into it. Sam was in concerned Dom mode and needed to make sure Dean was okay. And it settled Dean too, Sam’s voice soothing him even has his pointy fingers poked and prodded._ _

__“Well, I am pleased you were punished. Such cheek, Dean! It doesn’t matter who the boss is, if they are telling you you need to do something, you do it. _That_ is your job.”_ _

__“But it wasn’t appropriate, Sam!” Dean was being argumentative, but because Sammy needed it. At least that was the plan. He stopped though, when Sam had two fingers in his ass._ _

__“I’m going to fuck you tonight,” Sam decided. “My little princess has obviously forgotten how to behave, so I’ll remind you.”_ _

__Dean jumped as Sam’s giant hand laid smack after smack across his poor butt._ _

__“Sa-am,” he complained._ _

__Sam’s hand stopped. Dean tensed. That wasn’t how this normally went…_ _

__“Is that how you take discipline in this house? I don’t think so, Princess. Up with me.”_ _

__Dean was unceremoniously dragged up, momentum and Sam’s strong grip the only thing keeping him upright, as he tripped in on his pants._ _

__“Sam-“_ _

__Sam gripped Dean’s chin. “Is that how you talk to Daddy?”_ _

__Not that Dean had time to respond. Sam grabbed his hand, and Dean pouted the whole way to the study, where he was bent over Sam’s desk. Dean knew what was coming, but Sam decided to drag it out. Sadistic bastard!_ _

__“I’ve obviously been remiss, and my pretty princess is getting too big for his britches. Let me help you remember that I expect you to always be on your best behaviour.”_ _

__There was a moment of silence before the whistle of the strap as it moved through the air, followed by an almighty _crack_. _ _

__“Ahhhh! One, thank you sir!”_ _

__Dean couldn’t help but tense his buttocks – fuck he was out of practice! – as the strap whistled through the air again._ _

__“Twoooooo! Thank you, sir!”_ _

__Another 45 landed with painful precision before Sam stopped to survey his handywork. Dean was a blubbery mess._ _

__“Oh baby, such a sore looking bottom. Just a few more and then we’ll be done.”_ _

__“Sam- _Sir_! I meant _Sir_ , Daddy!” Dean was quick to correct himself, but it was too late. _ _

__“The last three will teach you respect, young man. Hold your cheeks open, Princess.”_ _

__Taking in a trembling breath, Dean shook his head no, but his hands were already obedient, reaching back to spread himself wide for his dom._ _

__“Here’s what’s going to happen.” Sam’s - _Daddy’s_ \- voice, was dark with lust. “These final three will go directly on your slutty little hole. Then you’ll keep holding yourself open while Daddy fucks you, to remind you _exactly_ who you belong to. And tomorrow you go to your boss, and tell them that you Dom is giving them permission to strap your naughty little bottom. And I will be checking after work on Friday to make sure that you’ve followed through.”_ _

__One part of Dean’s brain was rejoicing! He wouldn’t need to find an explanation for Sam after Michael punished him on Friday. The bigger part was smart and already answering Daddy._ _

__“Thank you, Daddy, for reminding me how to behave.”_ _

__Daddy flicked one sore ass cheek._ _

__“Remind who how to behave?”_ _

__Dean sniffled. He hated this part as much as he loved it. “Thank you for reminding your pretty princess how to behave.”_ _

__“Good boy.” Sam’s voice was warm. “You don’t have to count these last ones, Princess.”_ _

__Which was pretty fucking fortunate, because even though Dean had been a good boy, Daddy didn’t hold back. After the first stripe, fire burnt through Dean’s sensitive parts, and with a cry he let go._ _

__“No, no, no. Back into position, Princess. I’d work harder to stay in position, if I was you. Don’t want me to hit these instead.”_ _

__Dean froze as Daddy tapped the strap against his balls._ _

__Somehow Dean stayed in position, even though the second hurt worse than the first._ _

__“Good boy. Last one.”_ _

__It hurt as much as the others, but it also sent him to that floaty place. He let go of his cheeks, only to have Daddy’s hand down on his, keeping them there._ _

__“No, baby. Hold yourself open for Daddy.”_ _

__Muffling a sob into Daddy’s desk, Dean did as he was asked. And Daddy felt big – even bigger than he normally did! Dean’s hole was so hot and tight and sore. Daddy pushed all the way in, not waiting for Dean. He didn’t stop until his heavy balls were resting against Dean’s aching ass._ _

__“This is for Daddy, Princess. No coming, or Daddy will be _very_ unhappy with you.”_ _

__That was pretty much the only warning Dean had before Daddy drew back and slammed in, balls deep. Luckily Daddy had stretched him earlier, so while it wasn’t comfortable it wasn’t the _worst_. The truth was, this sent Dean to his very happy, very floaty place… _ _

__“Such a sweet pussy, Princess. Perfect for Daddy. So hot and tight. Been too empty, baby, I know, I know. Don’t worry, Daddy will fill you right up.”_ _

__Daddy had obviously been holding back, because he’d barely finished speaking before he painting Dean’s insides with his come. He ground against Dean until his cock emptied, before sighing and dropping forward, his body big and heavy over Dean._ _

__“Good boy. Keep holding those cheeks while I get a plug.”_ _

__Daddy slipped out, and Dean clenched as hard as he could. Daddy would be very unimpressed if Dean let his come drip out._ _

__“There’s my good boy.”_ _

__Daddy was back, running a soothing hand down around the curve of Dean’s hip, before pushing a plug in, then dropping a dropping a light smack down on the base of the plug. Dean squawked._ _

__“Daddy!”_ _

__Chuckling, Daddy pulled Dean up, before taking them both to the bedroom. Soon they were both settled in bed, Dam nestled up close to Dean, his soft cock nestled between Dean’s hot, sore ass cheeks._ _

__“Thank you, Princess.”_ _

__Dean asleep to Sam stroking his hair._ _


	5. Michael (Part 2)

**Summary for the Chapter:**

> The rest of the week with Michael

**Notes for the Chapter:**

> Oh hey bet you weren’t expecting this! Given that the last chapter was meant to be Michael… there wasn’t enough of him in it. And since I am writing this story mainly for Mock, and Michael is her fave, there has to be more. 
> 
> Also, heya! Man has lockdown been emotionally exhausting! I am also looking for a new job, as I am one of the ones whose contact will not be continuing because of covid – woo! (that’s sarcasm btw). I have been working hard and watching anime, and I got inspired so hard, so I have posted a few Kuroko no Basuke fics, and I have more to come. And I will probably end up writing Haikyuu!! as well. I think SPN has spoilt me for kinky fics. So even though KnB is not very active, and Haikyuu is ridiculously sweet, I will add to those. Different characters same kinks ;-) and with that in mind, please enjoy this latest installment

“Remember your boss has permission to strap your naughty little ass this week. By Friday, Dean, and I will be checking.”

Sam sent him out the door with an almighty _whack_ to his very tender ass. 

“Ow!” Dean complained. 

Sam simply raised an eyebrow. Sensibly, Dean kissed his Dom goodbye and without another word left for the day. 

~o~

“Right on time, Mr. Winchester.”

“Sir,” Dean greeted his chipper boss. Who was looking damn fine. Really damn fine. “Ummmm. Are we doing something today?”

Always a snazzy dresser, Michael looked _amazing_. His dark blue suit had a sheen that Dean only recognized because of yesterdays torture. The waistcoat followed the fine lines of Michael’s body, and instead of a tie he was wearing a… scarf? A masculine scarf, which even to Dean’s untrained eye looked good. In fact, Michael looked drool worthy, and Dean wouldn’t mind seeing him strip that sexy suit of his sexy body and-

Dean accidentally made eye contact, and Michael smirked. Smug asshole. 

“So you _can_ tell the difference between quality suits. I did wonder after yesterday’s little tantrum.”

Opening his mouth to argue, Dean thought the better of it and shut it. Michael’s smirk intensified. 

“I’ve ordered you five suits, with suitable accessories and accompaniments. Don’t worry,” Michael held up a hand, forestalling Dean’s new complaint. “You will never have to put the outfit together, but you _will_ wear what you are told.”

Michael held Dean’s gaze, daring him to argue. Dean, despite what everyone seemed to think, was not an idiot, and he dropped his eyes and nodded obediently. He didn’t have to like it, but if it was part of the job, he’d do it. 

“Good! I had them deliver the cobalt blue suit, with the green tie and the purple shirt.”

Dean blanched, but Michael just smiled. 

“Don’t worry, you’re going to look fabulous.”

~o~

It was amazing the difference a good suit made. Michael took him to _Velocity_ , just the most expensive and exclusive dining establishment in the city. He knew of it, of course. All the directors went there for their most important meetings, with the richest, and most prestigious clients. 

And here Dean was, and he didn’t even feel out of place! 

“Fergus, how good to see you. Is Rowena busy today?”

Th man, Fergus, resplendent in a subtly shiny black suit that _screamed_ money, had accessorised with a red tie and a matching pocket handkerchief (probably silk, a newly skilled Dean noted). On Fergus, it was a douche look, but Dean could see on the right person, like Michael… or perhaps Sam… it would look nothing short of amazing. 

“Mother is busy today. Although she will be oh so sorry to have missed your new associate. I’m sorry I don’t think I’ve met you before Mr…”

The douchebag, who had reached for Dean’s hand and taken it in his slightly clammy one, trailed off, but Dean knew how to deal with his sort. 

“Winchester,” Dean replied with a stunning smile. “And it’s a pleasure to meet you, Fergus.” 

Michael spluttered, obviously covering a laugh, and Fergus’ eyes narrowed before he sent Michael a fairly smarmy smirk. And he still hadn’t let go of Dean’s hand. 

“Oh, he is charming isn’t he. I prefer Crowley, Mr Winchester. No Mister, just Crowley.”

Dean squeezed Fergus’ – no, _Crowley’s_ \- hand a little harder. Not enough to antagonise, just enough to inform him that he was overstepping some boundaries… 

“Then you must call me Dean.”

~o~

The rest of the week passed in much the same way. And Dean loved every second of it! He’d always been good in sales, good at talking to people, and winning them over (with honesty of course!), but this was so different. This was exciting! It was the thrust and parry of privilege, and Dean felt like he was an equal. Admittedly this was because Michael was there, and that meant these were real meeting, where real power was exchanged and real promises were extracted.

It was fucking exhilarating. 

~o~

By the time Friday rolled around, Dean was almost sorry to see the end of his placement. They’d spent the day organising details for the contracts, before Michael packed it all away and called him in for a debrief. 

It had been intense, but Dean felt… fuck! He felt valued, like he’d made a real difference. 

At the end of the conversation, Dean stood up to shake Michael’s hand farewell. Instead, Michael stopped him. As Dean politely waited, Michael reached backwards, opened his top drawer and pulled out a strap. Silently he laid it on his now very clean and clear desk. 

Face blank, inside Dean was all judgement. Top drawer? What a dramatic ass! No one seriously kept a strap in their top drawer. At least not at work. At home, Sam had lots of interesting things in top drawers… 

“It’s been quite the week, Dean. Quote the week indeed. I promised you at the start of the week you would be receiving a strapping, and how it turned out would be up to you, influenced by your behaviour and your choices.”

Ah fuck. Dean had actually forgotten about that. And really? He blamed Sam. Sam had warmed his bruised and marked bottom every morning, sending him to work with instructions to behave. And it worked! He’d been really good. Unfortunately, it made him feel like he’d already paid his penance. 

Although, now that he thought about it, this was good! He’d forgotten that Sammy had also told him to get his boss to strap him, and of course that hadn’t been on Dean’s priority list. But Sam would be checking tonight, to make sure he’d followed through with Sam’s instructions. Fuck… Dean was actually incredibly lucky! Right now he couldn’t sink into his relief. Because right now Michael was awaiting a response. 

“Yes Sir, I do remember.” It was only a little lie. He did remember, just after Michael reminded him. “I… I feel like I have been well behaved this week.”

Mainly, he added silently. 

Michael eyed him, before nodding. 

“On the whole I agree with you. Other than that certain temper tantrum when you were getting your suit fitting.”

Dean blushed. Yeah that had been pretty bad. 

“I then I wasn’t overly taken with the way you flirted at the hotel to get free drinks.”

“I can’t help that!” Dean defended himself. “That’s just what I do naturally.”

 _Naturally_ , Michael pinned him with a stern look. “Nor when you are representing Milton’s, it’s not. And I wonder what your Dom would have to say about it.”

Dean blanched. A lot. Sam would have a _lot_ to say abut Dean flirting. 

“That’s what I thought.”

Michael let the silence grow. Dean jumped when he finally spoke. 

“However, other than those… minor… infractions, I have been very impressed. You are quick, have a good work ethic, a good memory for detail, and are exceptionally skilled at finding out what people want.” Michael paused for a moment, and when he continued, he was more talking to himself than Dean. “Perhaps because you are such an extreme sub?”

Dean bristled, and Michael waved a lazy hand in his direction. 

“Stand down, Winchester. There is nothing wrong with mentioning your designation. It impacts with how you interact with people. Although I am adding that to your punishment.”

“What? Why?” Dean was pissed off. 

“This reaction to me mentioning your designation. It’s uncalled for. And that attitude is going to set you back. Take me. I don’t feel the need to overcompensate because I’m a mid-level dom.”

Dean glowered at the floor. It was totally different! 

“And people _will_ mention your designation. Such a reaction is a weakness.”

Well, yeah. Dean knew that! Being such a fucking subby sub _was_ a weakness. It wasn’t worth the argument though. Dean had had many a long conversation with Sam and they never ended well for him. 

Michael eyed him for a moment, the straightened up. “Right. I believe that is our discussion finished. Over here, Winchester.”

Michael moved over back to the sofa – and that was pretentious as all fuck having a sofa in your office. When Dean reached him, Michael had Dean’s trousers and panties down, and bent him over the arm of the couch. Adjusting himself a little, Dean set his arms against the pillows. Hearing Michael’s soft gasp, Dean looked back. Michael was smiling, eyes dancing, as he took in the lines and bruises that covered Dean’s ass. 

“Oh my. Someone has been a naughty boy. And by the look of these many, many bruises, continues to be a naughty boy.”

Yeah, yeah. Dean could definitely hear the smirk in Michael’s voice. 

“Well, let’s add to this lovely collection. No need to count – I will keep track. I want you to think about how you could behave in the future.”

Resting one firm hand on the small of Dean’s back, he wasted no time in peppering heavy sways over Dean’s ass and down his thighs. It wasn’t a long spanking, but it was just enough to warm him up, alighting the sting in his already abused ass. It would make what was to come feel worse, Dean bet.

“That’s enough of a warm up I think.”

Michael’s voice was cheery, but the feel of the strap against his behind was all business. Damn Dean hated being right! Stupid, sadistic doms. 

“Stay in position.” 

It wasn’t much of a warning, Dean thought, as Michael started in. He was stoic for the first ten, feeling the heavy weight against his already bruised flesh, but when Michael caught the crease of where his ass met his thigh, he went up on his toes and cried out.

“Motherfuc-“

“Keep still, Dean.”

This time there was no levity in Michael’s voice. And it was the start of his torture, as Michael laid stripe after careful strip from the top of his buttocks to the bottom of his thighs. Dean shoved his face into the pillows, both hiding his tears, and trying to keep his body as still as possible. Fucking hell! After this, Dean wouldn’t be able to sit down for a week! 

It went on and on and by the time Michael put the strap down, Dean’s legs were shaking with the effort of keeping himself up, and his face was a mess of tears and snot. Pressing a centring hand in the small of Dean’s back, Michael waiting while Dean gasped like a fucking fish until he got his breathing under control. Dean accepted the comfort. 

“Good boy. Such a good boy, Dean. You took that so well. You are forgiven. For your tardiness, for your tantrums, and for your sass. You are such a good boy, Dean.”

It was almost a jolt to remember how this all started. The week had been so amazing, so challenging and inspiring and just… amazing… that he’d actually forgotten how he’d ended up working with Michael! Abruptly Dean felt miserable. Because yeah… he was only here for now. It was never meant to last. It was just careful owners keeping a close eye on an employee who didn’t come up to scratch. _Stop thinking like that!_ , he snapped at himself. There was no point thinking like that. He had to pull himself together, and he tried to, before Michael noticed anything. But somehow Michael figured out something was going on. 

Probably wasn’t that hard, Dean thought ruefully. He was a goddamn mess. 

“Ah I can see you are worried and uncertain. But never you fear. You were so wonderful to work with, Dean. So promising. And I can promise _you_ , it won’t be the last time we work together.”

It wasn’t much, but it did help a little bit. When Dean finally looked up, Michael was smiling at him. 

“There’s my good boy. You have been wonderful, Dean. A real pleasure to work with. You noticed a few things that I missed, and I think we made a great team! Make sure to tell your Dom that you made me proud.”

Dean cursed his stupid inner glow at the praise. Still. That helped too. He could feel himself coming together. 

“Now, I will give you an early mark, but right now I want you get that bare bottom of yours to that corner. Fifteen minutes, and then I’ll send you home.”

Dean who had finally made it upright, and was in process of pulling up his pants, froze. He turned beseeching eyes on Michael, who just laughed. 

“None of that, none of that. That corner, now. Hands behind your head, and your naughty red bottom facing me. You may have been a good boy this week, but let’s not forget that you are here because of your tardiness. Quick steps, Dean.”

Dean’s steps were only moderately quick. 

~o~

Dean hated corner time. Hated it with a passion. And wasn’t like he wasn’t experienced in staring at a blank wall, but it still didn’t mean he liked it. It also didn’t mean it didn’t work, and by the time someone knocked on Michael’s door, he barely registered the new person’s entry. That was until he heard Cas’s dark tones. 

“Oh good, you’re still here. Crowley had been on the phone and wants to continue working on the project.”

“Excellent! I think we can thank Dean for that! He really did a wonderful job at the lunch with Crowley.”

“Is that so? Well done, Dean.”

While Castiel’s voice was warm and inviting, Dean wasn’t stupid enough to turn around. And he wasn’t stupid enough to ignore the voice’s owner either. His ass had definitely had enough punishment for the week! Month really…

With that in mind, his “Thank you, sir” was very demure. 

Castiel laughed. “I see you’ve spanked some manners into him.”

“For now.” Dean could hear the laughter in Michael’s voice as well. “Ok, my good boy, pants up and come here.”

Wondering what other torments awaited him, Dean was pleasantly surprised to find it was a hug. That wasn’t so bad. 

“Thank you for your hard work this week, Dean. Next week you’ll be working with Gabriel. Please arrive at his office at-“

“Ten,” interrupted Castiel. “On Monday you may arrive at ten, and after that you will work with Gabriel as he sees fit. Have a pleasant weekend, Dean.”

Taking his leave – a whole hour early! – Dean was home just after Sam. 

“In the kitchen, Dean. Go have a shower and get dressed in what I laid out on the bed, and then join me here.”

Ugh. Sam sounded firm, and Dean wasn’t in the mood for another spanking. Plus, a shower sounded good. So it was less than twenty minutes later that Dean was wandering back into the kitchen, comfy in loose sweats and a t-shirt. 

“Come here, baby.”

Sam held out an imperious hand, and Dean went willingly. Sam kissed him hard, and Dean melted under his touch. But before he could get too comfortable, Sam spun him around, pulling his sweatpants down. 

“Oh my…” 

Dean could hear the lust in Sam’s voice. 

“That looks very sore, baby. Very sore, and very sexy.”

Sam moved his hands, although Dean stayed bent over with his pants around his knees. It took a few moments, but Sam put something in the oven, and Dean could hear the beeps as Sam set the timer. Then he was back, pulling up Dean’s pants, and ushering him towards the bedroom. 

“We have an hour for me to show you how much I enjoy those stripes on your ass.”

**Notes for the Chapter:**

> (did I also mention the reason this is late is because I had this chapter written out, but then I dropped my notebook in my workmates car, and because of lockdown it took me months to get back. no? well that is part of my reason, and I am sticking to it!)

**Author's Note:**

> Please feel free to let me know what you think :)


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